CN104072472A - Preparation method of plagiochin E - Google Patents

Preparation method of plagiochin E Download PDF

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Publication number
CN104072472A
CN104072472A CN201410266314.6A CN201410266314A CN104072472A CN 104072472 A CN104072472 A CN 104072472A CN 201410266314 A CN201410266314 A CN 201410266314A CN 104072472 A CN104072472 A CN 104072472A
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China
Prior art keywords
plagiochin
extraction
preparation
phase
acetone
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CN201410266314.6A
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Chinese (zh)
Inventor
刘东锋
杨成东
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Nanjing Zelang Medical Technology Co Ltd
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Nanjing Zelang Medical Technology Co Ltd
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Priority to CN201410266314.6A priority Critical patent/CN104072472A/en
Publication of CN104072472A publication Critical patent/CN104072472A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to a preparation method of plagiochin E. The preparation method of plagiochin E is characterized by comprising the following steps: crushing dried marchantia polymorpha, extracting grease materials out of the dried marchantia polymorpha by using a supercritical carbon dioxide extraction method, extracting degreased materials through a flash extraction method by using hydrous ethanol as an extraction solvent, concentrating the extraction solution to obtain extract, then adding acetone and dipotassium phosphate double-aqueous-phase system according to a ratio, uniformly mixing, dividing the system into an upper phase and a lower phase, taking out acetone phase rich in plagiochin E, adding an inorganic salt solution, uniformly mixing, extracting by using ethyl acetate, separating out an ethyl acetate layer rich in plagiochin E, performing vacuum concentration, and drying the concentrated extract in vacuum to obtain the plagiochin E. By virtue of the preparation method of plagiochin E, the production process is simplified, a high extraction rate is achieved, the production process is low in energy consumption, hardly causes pollution and is suitable for industrial production.

Description

A kind of preparation method of Plagiochin E
Technical field
The invention belongs to pharmaceutical technology field, relate to a kind of preparation method of Plagiochin E.
Background technology
Plagiochin E (Plagiochin E) is that with herb, molecular formula is C from moss Marchantiaceae marchantia marchantia Marchantia polymorpha L. 28h 24o 4, molecular weight is 424, structural formula is
Modern study shows, Plagiochin E has anti-mycotic activity, and Candida albicans is had to good anti-mycotic activity, and its MIC=16 μ g/ml, shows identical anti-mycotic activity to fluconazole Resistant strain, is a kind of potential antibiotic preparation and reverses antifungal agent resistance agent.
By literature search, the industrial extraction method relevant report of domestic rarely found Plagiochin E.Chinese patent " a kind of Bibenzyl compound Plagiochin E and extraction and separation method and application " (application number is 200410036045.0), a kind of extraction and separation method of Plagiochin E is disclosed, key step is: ether or methyl alcohol lixiviate, silica gel column chromatography, it is long that this invents the described extraction and separation method cycle, yield is low, is unfavorable for suitability for industrialized production.Therefore, work out a kind of method of preparing Plagiochin E and be very important, for the comprehensive utilization tool that expands medicine source and dry marchantia, have very important significance.
Summary of the invention
For fear of the deficiencies in the prior art part, the invention provides a kind of preparation method of Plagiochin E, utilize aqueous two phase extraction technique, not only improve the extraction yield of Plagiochin E, and simplified operation, economy is applicable to again suitability for industrialized production.
In order to solve the problems of the technologies described above, the present invention by the following technical solutions:
(1) dry marchantia is pulverized, adopted super critical CO 2 technology extraction oil lipid material;
(2) degreasing thing extracts with ethanolic soln, obtains extracting solution;
(3) extracting solution concentrates to obtain medicinal extract, then adds in proportion acetone and dipotassium hydrogen phosphate aqueous two-phase system to mix, and at room temperature standing 2 ~ 5h, is divided into upper and lower two-phase;
(4) take out the acetone phase be rich in Plagiochin E, add inorganic salt solution and mix, then adopt and be extracted with ethyl acetate, isolate the ethyl acetate layer that is rich in Plagiochin E and carry out concentrating under reduced pressure, vacuum-drying, obtains off-white powder shape Plagiochin E.
In described step (1), supercritical carbon dioxide extraction pressure is 20 ~ 35MPa, and extraction temperature is 35 ~ 50 ℃, extraction 0.5 ~ 2h.
In described step (2), degreasing thing is placed in flash extracter, adds 55 ~ 75% ethanolic solns of 5 ~ 8 times of amount volumes of raw materials quality for extracting solvent, carries out flash extraction 1 ~ 3 time, and each 5 ~ 15min, filters and obtain extracting solution;
In described step (3), flash extraction voltage is 140 ~ 160V, and extraction time is 60s ~ 100s.
In described step (3), acetone add-on is 1/2 ~ 4/5(V/V of medicinal extract volume), dipotassium hydrogen phosphate add-on is 15 ~ 30%(W/V of total liquid volume amount).
In described step (4), inorganic salt solution is 3 ~ 5% sodium chloride solutions.
The invention has the beneficial effects as follows: adopt supercritical carbon dioxide extraction method to remove oil substances, fast, efficiently; Adopt flash extraction method, rapidly and efficiently, low power consuming, environmental protection; The present invention utilizes the technology of aqueous two-phase extraction to prepare Plagiochin E, and the method is compared with in the past traditional silica gel column chromatography, macroporous adsorption resin chromatography method, has that treatment capacity is large, technical process is short, can carry out operate continuously, separation efficiency advantages of higher.
Below in conjunction with embodiment, further illustrate the present invention, but the scope of protection of present invention is not limited to following embodiment.
Embodiment
Embodiment 1:
Get the dry marchantia pulverizing medicinal materials of 1kg, be placed in extraction kettle, adopt overcritical degreasing, extraction temperature is 35 ℃, pressure is 25MPa, extraction time is 1h, degreasing thing is placed in flash extracter, add 5L75% ethanolic soln for extracting solvent, extraction voltage is 140V, extraction time is 90s, carry out flash extraction 1 time, extract 15min, extracting solution concentrating under reduced pressure obtains medicinal extract, in medicinal extract, add 1/2(V/V) acetone, dipotassium hydrogen phosphate, mix, make dipotassium hydrogen phosphate quality in formed two phase aqueous extraction system account for 15% of total liquid volume amount, in 50 ℃ of water-bath 1h, constantly jolting during this time, then the standing 2h phase-splitting of room temperature, phase on the acetone of Plagiochin E is rich in taking-up, add 5% sodium chloride solution precipitating, adopt again 2 times of amount ethyl acetate extraction 4 times, isolate the ethyl acetate layer that is rich in Plagiochin E and carry out concentrating under reduced pressure, concentrated extract vacuum-drying at 70 ℃, obtain Plagiochin E 3.5g, content 80.57%, UV, IR, MS, 2hNMR, 13the data of its physical behavior of the sign such as CNMR are consistent with prior art.
Embodiment 2:
Get the dry marchantia pulverizing medicinal materials of 1kg, be placed in extraction kettle, adopt overcritical degreasing, extraction extraction temperature is 45 ℃, pressure is 20MPa, extraction time is 0.5h, degreasing thing is placed in flash extracter, add 8L65% ethanolic soln for extracting solvent, extraction voltage is 160V, extraction time is 100s, carry out flash extraction 2 times, each 10min, extracting solution concentrating under reduced pressure obtains medicinal extract, in medicinal extract, add 4/5(V/V) acetone, dipotassium hydrogen phosphate, mix, make dipotassium hydrogen phosphate quality in formed two phase aqueous extraction system account for 20% of total liquid volume amount, in 50 ℃ of water-bath 1h, constantly jolting during this time, then the standing 5h phase-splitting of room temperature, phase on the acetone of Plagiochin E is rich in taking-up, add 3% sodium chloride solution precipitating, adopt again 3 times of amount ethyl acetate extraction 2 times, isolate the ethyl acetate layer that is rich in Plagiochin E and carry out concentrating under reduced pressure, concentrated extract vacuum-drying at 80 ℃, obtain Plagiochin E 2.9g, content 88.66%, UV, IR, MS, 2hNMR, 13the data of its physical behavior of the sign such as CNMR are consistent with prior art.
Embodiment 3:
Get the dry marchantia pulverizing medicinal materials of 1kg, be placed in extraction kettle, adopt overcritical degreasing, extraction temperature is 30 ℃, pressure is 30MPa, extraction time is 2h, degreasing thing is placed in flash extracter, add 7L55% ethanolic soln for extracting solvent, extraction voltage is 150V, extraction time is 60s, carry out flash extraction 3 times, each 5min, extracting solution concentrating under reduced pressure obtains medicinal extract, in medicinal extract, add 2/3(V/V) acetone, dipotassium hydrogen phosphate, mix, make dipotassium hydrogen phosphate quality in formed two phase aqueous extraction system account for 25% of total liquid volume amount, in 50 ℃ of water-bath 1h, constantly jolting during this time, then the standing 3h phase-splitting of room temperature, phase on the acetone of Plagiochin E is rich in taking-up, add 4% sodium chloride solution precipitating, adopt again 1 times of amount ethyl acetate extraction 3 times, isolate the ethyl acetate layer that is rich in Plagiochin E and carry out concentrating under reduced pressure, concentrated extract vacuum-drying at 75 ℃, obtain Plagiochin E 3.4g, content 83.45%, UV, IR, MS, 2hNMR, 13the data of its physical behavior of the sign such as CNMR are consistent with prior art.
Embodiment 4:
Get the dry marchantia pulverizing medicinal materials of 1kg, be placed in extraction kettle, adopt overcritical degreasing, extraction temperature is 50 ℃, pressure is 35MPa, extraction time is 1h, degreasing thing is placed in flash extracter, add 7L75% ethanolic soln for extracting solvent, extraction voltage is 150V, extraction time is 90s, carry out flash extraction 3 times, each 10min, extracting solution concentrating under reduced pressure obtains medicinal extract, in medicinal extract, add 4/7(V/V) acetone, dipotassium hydrogen phosphate, mix, make dipotassium hydrogen phosphate quality in formed two phase aqueous extraction system account for 30% of total liquid volume amount, in 50 ℃ of water-bath 1h, constantly jolting during this time, then the standing 4h phase-splitting of room temperature, phase on the acetone of Plagiochin E is rich in taking-up, add 5% sodium chloride solution precipitating, adopt again 3 times of amount ethyl acetate extraction 2 times, isolate the ethyl acetate layer that is rich in Plagiochin E and carry out concentrating under reduced pressure, concentrated extract vacuum-drying at 70 ℃, obtain Plagiochin E 2.8g, content 80.32%, UV, IR, MS, 2hNMR, 13the data of its physical behavior of the sign such as CNMR are consistent with prior art.

Claims (6)

1. a preparation method for Plagiochin E, is characterized in that:
(1) dry marchantia is dried, pulverized, adopt super critical CO 2 technology extraction oil lipid material;
(2) degreasing thing extracts with ethanolic soln, obtains extracting solution;
(3) extracting solution concentrates to obtain medicinal extract, then adds in proportion acetone and dipotassium hydrogen phosphate aqueous two-phase system to mix, and at room temperature standing 2 ~ 5h, is divided into upper and lower two-phase;
(4) take out the acetone phase be rich in Plagiochin E, add inorganic salt solution and mix, then adopt and be extracted with ethyl acetate, isolate the ethyl acetate layer that is rich in Plagiochin E and carry out concentrating under reduced pressure, vacuum-drying, obtains off-white powder shape Plagiochin E.
2. the preparation method of Plagiochin E as claimed in claim 1, is characterized in that: in described step (1), supercritical carbon dioxide extraction pressure is 20 ~ 35MPa, and extraction temperature is 35 ~ 50 ℃, extraction 0.5 ~ 2h.
3. the preparation method of Plagiochin E as claimed in claim 1, it is characterized in that: in described step (2), degreasing thing is placed in flash extracter, add 55 ~ 75% ethanolic solns of 5 ~ 8 times of amount volumes of raw materials quality for extracting solvent, carry out flash extraction 1 ~ 3 time, each 5 ~ 15min, filters and obtains extracting solution.
4. the preparation method of Plagiochin E as claimed in claim 3, is characterized in that: in described step (3), flash extraction voltage is 140 ~ 160V, and extraction time is 60s ~ 100s.
5. the preparation method of Plagiochin E as claimed in claim 1, is characterized in that: in described step (3), acetone add-on is 1/2 ~ 4/5(V/V of medicinal extract volume), dipotassium hydrogen phosphate add-on is 15 ~ 30%(W/V of total liquid volume amount).
6. the preparation method of Plagiochin E as claimed in claim 1, is characterized in that: in described step (4), inorganic salt solution is 3 ~ 5% sodium chloride solutions.
CN201410266314.6A 2014-06-16 2014-06-16 Preparation method of plagiochin E Pending CN104072472A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2918021A1 (en) * 2021-01-13 2022-07-13 Consejo Superior Investigacion Excerpt from a marching plant and Polymorpha Subp. and its uses (Machine-translation by Google Translate, not legally binding)
CN115650946A (en) * 2022-04-08 2023-01-31 南通大学 Bibenzyl derivative and preparation method and application thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2918021A1 (en) * 2021-01-13 2022-07-13 Consejo Superior Investigacion Excerpt from a marching plant and Polymorpha Subp. and its uses (Machine-translation by Google Translate, not legally binding)
CN115650946A (en) * 2022-04-08 2023-01-31 南通大学 Bibenzyl derivative and preparation method and application thereof

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